Winter Haven Rentals
- From $366 per night (USD)
VRBO
Awesome Lake House With Private Dock, Canoe, Kayaks, Game-Room, & Lots To Do!!!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Awesome lake house, with a private dock, kayaks, a canoe, a game room with foosball, air hockey/small pool table, an arc ...
From $366 per night (USD)VRBO
- From $110 per night (USD)
Expedia
Serenity Retreat, Confidently Clean
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This is a unique 2 story antique building that has been completely renovated and sectioned into 2 small apartments on t ...
From $110 per night (USD)Expedia
- From $394 per night (USD)
VRBO
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Lake Silver Retreat III is a home with options ~ you can rent it as a 3 bedroom or a 5 bedroom (some holidays exclusions ...
From $394 per night (USD)VRBO
- From $99 per night (USD)
Expedia
*Modern Tiny Lake Cottage*AceLoc*4miles*LEGOLAND*
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
WELCOME! Lake Mariam Tiny Home sits on 2.6 acres of Lakefront Property. If hospitality & peace is what you want, our spa ...
From $99 per night (USD)Expedia
- From $350 per night (USD)
VRBO
Lake Idylwild Delight: Waterfront Lakehouse, Private Dock, Tiki Bar, Kid's Jungle Gym, Near Legoland
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to SUNRISE ON LAKE IDYLWILD! This home has something special for everyone in your family. This beautifully dec ...
From $350 per night (USD)VRBO
- Click For Pricing
Expedia
Lake Lucerne way villa
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Villa Lake Lucerne, located just around 30 minutes from the Disney World Resort and 17 minutes from the LEGO- ...
Click For PricingExpedia
- From $99 per night (USD)
VRBO
Soak up the charm of this cozy, recently remodel studio.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This studio is located minutes from Downtown Winter Haven, one of Florida's oldest towns. The small downtown is packed ...
From $99 per night (USD)VRBO
- From $132 per night (USD)
Expedia
Modern HouseBoat*AceLoca*4Miles*LegoLand*
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to the SeaRover on Lake Mariam part of the Chain of Lakes! This is a fully furnished newly renovated house boat ...
From $132 per night (USD)Expedia
- From $468 per night (USD)
VRBO
Fantastic Water Front Home on the Chain of Lakes
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
We are sharing our dream home with you! This home offers one of the best open layouts in Winter Haven. Great open kitche ...
From $468 per night (USD)VRBO
- From $114 per night (USD)
Expedia
Confidently Clean, Quint & Cozy Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
This is a unique 2 story antique building that has been completely renovated into 4 small apartments. This property was ...
From $114 per night (USD)Expedia
- From $308 per night (USD)
VRBO
Lake life living 45 mins from most central FL theme parks...
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Older home very spacious 3 bedrooms, 3 baths large back porch looking over the pool as well as Lake Shipp also on the c ...
From $308 per night (USD)VRBO
- From $579 per night (USD)
Expedia
Lakefront Luxury: Boat Dock, Pet-Friendly, Close to LegoLand, Perfect for Family Fun
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Ready for some Lake with a New Dock & Lego fun - Lake Silver Retreat in the Heart of the City will take your breath away ...
From $579 per night (USD)Expedia
- From $262 per night (USD)
VRBO
Historic, private, updated, 5 Bedroom Plantation Home, lake, fishing, leasure\n
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy your stay in this Historic, large, peaceful, fully renovated Plantation home. This home consists of 5 bedrooms, 3 ...
From $262 per night (USD)VRBO
- From $112 per night (USD)
Expedia
Winter Haven Apt: 1 Mi to Polk State College!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Close to Polk State College, this convenient, vibrant vacation rental is great for prospective students and alumni, visi ...
From $112 per night (USD)Expedia
- From $130 per night (USD)
VRBO
Studio Apartment in Winter Haven, FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our studio apartment, a perfect retreat for solo travelers or couples seeking a comfortable and convenient pl ...
From $130 per night (USD)VRBO
- From $377 per night (USD)
Expedia
Peaceful Lakeside Retreat
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Tranquility awaits you at this beautiful lakefront home. We invite you to enjoy the best of Florida indoor/outdoor livi ...
From $377 per night (USD)Expedia
- From $206 per night (USD)
VRBO
Best sunsets in Winter Haven. Lakefront home 5 minutes from downtown!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy the best sunset in Winter Haven on a hammock, then drive 3 mins for dinner downtown. You can't beat this slice of ...
From $206 per night (USD)VRBO
- From $144 per night (USD)
Expedia
Comfortable bedroom and house to stay in w\/ swimming pool.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The bedroom i am renting is very comfortable, has tv, dresser, bistro table and chairs, floor lamp, two night stands wit ...
From $144 per night (USD)Expedia
- From $265 per night (USD)
VRBO
Carefree Cove on Lake Connie - With Hot Tub! 15 mins to Legoland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on the shores of Winter Haven's Lake Connie, this charming 3-bedroom promises a tranquil escape. This cozy lake ...
From $265 per night (USD)VRBO
- From $181 per night (USD)
Expedia
3br\/2ba Haven away from home w\/master suite, 6 mi. to Legoland & pet-friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Location, Location, Location ! Bring the whole family to this spacious home with lots of room for fun! Centrally locate ...
From $181 per night (USD)Expedia
- From $335 per night (USD)
VRBO
341 Legoland Sherman's Antiques Lake Silver
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Welcome to our charming home located in a peaceful neighborhood, perfect for families and small groups. This co ...
From $335 per night (USD)VRBO
- From $292 per night (USD)
Expedia
Lake House on the LEGOLAND Chain-of-Lakes with private beach and boat dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Stay comfortably in Central Florida at this 4-bedroom Lakefront Home on the Lego Land Chain-of-Lakes! With two Master Su ...
From $292 per night (USD)Expedia
- From $158 per night (USD)
VRBO
Family-Friendly Haven near Downtown - Fast Wifi
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Summary: Escape to our inviting 3-bedroom, 1-bath Family-Friendly Retreat near downtown Winter Haven, FL—a haven for fam ...
From $158 per night (USD)VRBO
- From $164 per night (USD)
Expedia
Cozy Winter Haven Escape | Pet-Friendly\/Fenced Lot
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Cozy Retreat near Legoland! Our charming 3-bedroom, 1-bath home offers a pullout sofa bed, a fully s ...
From $164 per night (USD)Expedia
- From $142 per night (USD)
VRBO
Tiny Paradise
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This Winter Haven studio boasts 1 inviting bedroom with a full bed. The space is equipped with essentials like WiFi, hea ...
From $142 per night (USD)VRBO
- From $324 per night (USD)
Expedia
15 minutes to Legoland- Serene Lakeside Cottage Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your serene escape in Winter Haven, just minutes away from the excitement of Legoland! This enchanting 3-bedr ...
From $324 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Spacious 4-bedroom Corporate Home with AC, WiFi in gorgeous Winter Haven
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Make yourself at home in this 4-bedroom Winter Haven retreat. This corporate, short or mid term rental home boasts beaut ...
From $144 per night (USD)VRBO
- From $585 per night (USD)
Expedia
6BR Lakefront Escape w\/ Heated Pool, Game Room, Fire Pit, Dock – Perfect for Family Gatherings & Fun
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Escape to Emerald Anchor Escape, a spacious 6-bedroom lakefront retreat in Winter Haven, designed for the ultimate famil ...
From $585 per night (USD)Expedia
- From $291 per night (USD)
VRBO
*3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1724
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
WELCOME! Lake Mariam Vacation Home (2) is part of a duplex built in 2016 that sits on 2.6 acres of Lakefront Property. I ...
From $291 per night (USD)VRBO
- From $164 per night (USD)
Expedia
*3\/2*GorgeousNEWLakeHome2AceLoc*4mi*LEGOLAND*1722
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
WELCOME! Lake Mariam Vacation Home (1), is part of a duplex that sits on 2.6 acres of Lakefront Property. There is also ...
From $164 per night (USD)Expedia
- From $168 per night (USD)
VRBO
CELEBRATE!! Sun, Fun, Relax- Suite- 2 Queen Beds
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
You’ll find the basic amenities like a microwave and refrigerator in every room. Our suites include a sofa bed and some ...
From $168 per night (USD)VRBO
- From $183 per night (USD)
VRBO
Amazing!!! WINTER HAVEN 2 Queen Beds fun 4 All
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Make the most of your time in Winter Haven with our amenities, which allow you to focus on the people and experiences th ...
From $183 per night (USD)VRBO
- From $187 per night (USD)
VRBO
Winter Haven-Historic property- N Legoland Sleep 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the great property. This historic property was the home of The Red Sox spring training for decades and the so ...
From $187 per night (USD)VRBO
- From $183 per night (USD)
VRBO
Fun and Relaxation in Winter Haven!! 2 Queen Beds,
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Our pet-friendly guest room offers free light breakfast item together with your choice of coffee, tea and juice to start ...
From $183 per night (USD)VRBO
- From $134 per night (USD)
VRBO
Charming Town House — 10 Minutes from the Legoland Park and Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This house is located a perfect distance from the best places in Winter Haven. It sits a ten minute drive from the Legol ...
From $134 per night (USD)VRBO
- From $263 per night (USD)
Expedia
Legoland 3 Bedroom Pet Friendly Pool Home
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 13
Bring the whole family to this great place with lots of room for fun. This home is conveniently located only 2.1 miles f ...
From $263 per night (USD)Expedia
- Click For Pricing
VRBO
Eagle Lake Home < 7 Mi to Legoland!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
A fun-filled family getaway awaits at this lovely Eagle Lake vacation rental! This 3-bedroom, 2-bathroom home provides e ...
Click For PricingVRBO
- From $103 per night (USD)
Expedia
Winter Haven Studio w\/ BBQ Grill: Steps to 2 Lakes
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience comfort and convenience at this quaint vacation rental in Winter Haven, FL! With quick access to restaurants, ...
From $103 per night (USD)Expedia
- From $130 per night (USD)
VRBO
4.4 miles to Legoland. Conveniently located near large highways and interstates.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
4.4 miles to Legoland. 36 miles to Disney (43 minutes) Cozy one bed one bath second floor condo. Centrally located. Walk ...
From $130 per night (USD)VRBO
- From $321 per night (USD)
Expedia
Spacious Modern 4bd\/2ba Home! Amazing Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Nestled in the Heart of Winter Haven, the Modern Home offers a remarkable fusion of innovation, convenience, and aesth ...
From $321 per night (USD)Expedia
- From $246 per night (USD)
VRBO
Serene, Cozy, Lakefront home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Cozy meets calm at this quaint lakefront home. We are located on the Chain of Lakes in Winter Haven, where the waterfr ...
From $246 per night (USD)VRBO
- From $180 per night (USD)
Expedia
Cozy 1-bedroom condo in delightful Winter Haven with AC, WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in Winter Haven, this welcoming condo features 1 bedroom with a tremendous king bed. Guests can enjoy the jetted ...
From $180 per night (USD)Expedia
- From $332 per night (USD)
VRBO
Getaway Clubhouse 5 mil Legoland & .5 mil Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a relaxing stay in this spacious and comfortable home, perfect for families or groups. The open layout of the livi ...
From $332 per night (USD)VRBO
- From $315 per night (USD)
Expedia
Sweet Cottage- 5 mi to Legoland & 0.5 mi to dwntwn
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This delightful lake-life inspired cottage includes 2 bedrooms and 1 ½ baths, a fooseball table, and easily sleeps 7 gue ...
From $315 per night (USD)Expedia
- From $95 per night (USD)
VRBO
The Unique cozy studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Super comfortable! Modern clean fully functioning. centrally located in Winter Haven. 1/2 mile to downtown, less than 4 ...
From $95 per night (USD)VRBO
- From $164 per night (USD)
Expedia
Cozy Bungalow - 5 mi Legoland & 0.5 mi Dwntwn
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This cozy bungalow includes 3 bedrooms and 1 ½ baths, and it sleeps up to 8 guests comfortably! Located approximately ...
From $164 per night (USD)Expedia
- From $314 per night (USD)
VRBO
The Old Haven - An Enduring Piece of Nostalgia
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
This charming home was built in 1908 and is located 45 minutes from Tampa/Orlando. Fully furnished, this space is perfe ...
From $314 per night (USD)VRBO
- From $487 per night (USD)
Expedia
Spacious 5-bedroom house with WiFi, AC in welcoming Winter Haven
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The Winter Haven home features five welcoming bedrooms, complete with two double beds and five single beds. It also incl ...
From $487 per night (USD)Expedia
- From $146 per night (USD)
VRBO
Cozy 1-Bedroom Retreat Near Downtown & Legoland
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to your perfect getaway! This charming one-bedroom unit offers all the essentials for a comfortable stay. The un ...
From $146 per night (USD)VRBO
- From $700 per night (USD)
Expedia
The Lakeview Oasis Getaway!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 21
Bring your family & friends and enjoy this amazing & relaxing lakefront view property with room for everyone to come tog ...
From $700 per night (USD)Expedia
- From $512 per night (USD)
VRBO
An Amazing Mid-Century Modern Experience
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Welcome to The Gene Leedy House, the life-long residence of iconic architect, Gene Leedy. A founding member of the Saras ...
From $512 per night (USD)VRBO
- From $110 per night (USD)
Expedia
Waterfront Vacation Rental on Lake Mirror!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 5
Situated directly on Lake Mirror, this charming Winter Haven vacation rental is perfect for snowbirds looking to embrace ...
From $110 per night (USD)Expedia
- From $250 per night (USD)
VRBO
Newly remodeled Vacation Home with Saltwater Pool
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This "brand-new" home, built in 2010, totally rebuilt and remodeled in 2022, is located in a gated community in the sout ...
From $250 per night (USD)VRBO
- From $124 per night (USD)
Expedia
Nice Private Studio Room — 10 Minutes from the Legoland Park and Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This private studio room is located a perfect distance from the best places in Winter Haven. It sits a ten minute drive ...
From $124 per night (USD)Expedia
- Click For Pricing
VRBO
Great Family Home Near Legoland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
About this space Your family will be close to everything when you stay at this centrally-located home near Legoland and ...
Click For PricingVRBO
- Click For Pricing
Expedia
Cozy Family Home Near Legoland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
About this space Relax with the fam after a fun day at LEGOLAND (4.7 miles) or Disney World (36 miles) in our newly reno ...
Click For PricingExpedia
- From $121 per night (USD)
VRBO
*CentralLocated*PrivateKingSuitew\/Bath, Washer&Dryer(Eagle)
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Centrally located Modern/Contemporary Spacious Private King Suite that is close to Winter Haven (WH) downtown (2 miles); ...
From $121 per night (USD)VRBO
- From $624 per night (USD)
Expedia
Dock & Lanai: Elegant Villa in Winter Haven!
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 8
WFH Friendly | Lake Access On-Site | 5,100 Sq Ft Escape to the ‘Water Ski Capital of the World’ at this Winter Haven va ...
From $624 per night (USD)Expedia
- From $171 per night (USD)
VRBO
Winter Haven Abode Near Lakes & Attractions
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy a relaxing escape to Winter Haven when you book this charming vacation rental home, complete with 2 bedrooms, 1.5 ...
From $171 per night (USD)VRBO
- From $237 per night (USD)
Expedia
Lakefront Home w\/ Screened Porch & Grill
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Living up to its city name, this elegant 3-bedroom, 3-bathroom Winter Haven home features the perfect haven for a relaxi ...
From $237 per night (USD)Expedia
- From $196 per night (USD)
VRBO
Lakefront house for rent
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 4
Million dollar lake view. Eagles nest in the back yard every year. No pets. No smoking. No children. No parties. Furnish ...
From $196 per night (USD)VRBO
- Click For Pricing
Expedia
PEACE & LOVE ROOM 5 Minutes from Winter Haven Florida
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This room is located 5 minutes from Winter Haven Hospital and is only designed to accommodate women, especially nurses a ...
Click For PricingExpedia
- Click For Pricing
VRBO
Peace & Love Room 5 minutes from Winter Haven Hospital
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Peace & Love Sanitized Private Room with private door entrance and bathroom. Wi-Fi, parking space for a Single person. V ...
Click For PricingVRBO
- From $98 per night (USD)
Expedia
TRAVELLING PROFESSIONALS ONLY - 3.3 miles to Winter Haven Hospital!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 1
This home is your home away from home. Quiet, clean, full paint job, all new furnishings, Roku TV in both bedrooms, Quee ...
From $98 per night (USD)Expedia
- Click For Pricing
VRBO
Lakeside Cottage in Lake Howard (Winter Haven Chain of Lakes)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Lakeside Cottage sits on Lake Howard, one of the most popular locations on "The Chain of Lakes" near downtown Winter ...
Click For PricingVRBO
- From $462 per night (USD)
Expedia
Luxury Home w\/ Lanai, Billiards, 6min to Legoland
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
CHECKOUT A FULL VIDEO OF THE PROPERTY: https://youtu.be/K6zlvwkvq-o ★ SPACIOUS 5-STAR LUXURY WINTER HAVEN HOME ★ You ...
From $462 per night (USD)Expedia
- From $96 per night (USD)
VRBO
Cute & Cozy 1 bedroom guesthouse located in Winter Haven FL
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The guesthouse Cute & Cozy is separate yet, it is adjacent to the main house (owner lives) and has its own entrance. L ...
From $96 per night (USD)VRBO
- Click For Pricing
Expedia
Beautiful 2bedroom near LEGoLAND
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Forget your worries in this spacious and serene space. This home is in a nice peaceful neighborhood near winter haven h ...
Click For PricingExpedia
- From $130 per night (USD)
VRBO
Luxury StayComfy at WinterHeaven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Have fun with the whole family at this two bedroom stylish place. Enjoy two comfy queen beds and a sofa-bed, tv 50'' wi ...
From $130 per night (USD)VRBO
- From $184 per night (USD)
Expedia
Cozy 1 BR Apt on Lake Howard with Lanai Patio, Dock & Kayaks
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Nestled along the tranquil shores of Lake Howard, this cozy studio apartment retreat offers breathtaking water views, mo ...
From $184 per night (USD)Expedia
- From $144 per night (USD)
VRBO
Vrbo Property
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our family-friendly home! Just a 5-minute walk to the nearest lake and a short 15-minute drive from Legoland, ...
From $144 per night (USD)VRBO
- From $453 per night (USD)
Expedia
Summer Specials! Pet Friendly, 7 Beds, Family Oasis
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Nestled on the west side of Lake Howard in Winter Haven, the Chain of Lakes Villa offers an enchanting retreat that cele ...
From $453 per night (USD)Expedia
- From $282 per night (USD)
VRBO
Winter Haven Home w\/ Pool Near Legoland!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Discover your next family getaway at 'Little Haven!' The modern 3-bedroom, 2-bathroom property provides a comfortable oa ...
From $282 per night (USD)VRBO
- From $531 per night (USD)
Expedia
Lakefront Winter Haven Retreat: Hot Tub & Patio!
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 22
Located just steps away from the pristine waters of the Chain of Lakes, this stunning 4-bedroom, 3.5-bathroom vacation r ...
From $531 per night (USD)Expedia
- From $170 per night (USD)
VRBO
Lakefront condo\n55+ community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Fully furnished. Bring only your clothing. Pool, shuffle board and dock for fishing. Sunroom included. Covered parking. ...
From $170 per night (USD)VRBO
- From $228 per night (USD)
Expedia
Lakefront 2 story 4\/2 bungalo with huge yard.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Property Description fully renovated lake front property with big back porch and yard flowing to the lake. The house has ...
From $228 per night (USD)Expedia
- From $93 per night (USD)
VRBO
Winter Haven Vacation Rental ~ 1 Mi to Downtown!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Encompassed by downtown attractions, sprawling lakes, and world-class theme parks, this 1-bed, 1-bath vacation rental in ...
From $93 per night (USD)VRBO
- From $364 per night (USD)
Expedia
Our Camp at Lake Cannon
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 12
Unbeatable Sunsets - relax @ the lake. Sleeps a Crowd Comfortably We pack in a lot of sleep space. Bunk room includes t ...
From $364 per night (USD)Expedia
- From $114 per night (USD)
VRBO
Quiet and cozy 55 plus community .
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 2
Great home in a 55 plus community setting. There are many areas of the home to enjoy. Sitting in the carport, soaking in ...
From $114 per night (USD)VRBO
- Click For Pricing
Expedia
4 Bedrm Central Home w\/Gameroom\n\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to this charming house in Winter Haven. This superb property boasts 4 queen beds spread across 4 cozy bedrooms, ...
Click For PricingExpedia
- Click For Pricing
VRBO
4 Bedroom, Legoland, Pet Friendly, Pool, Gameroom\n\n
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 15
This enjoyable house in Winter Haven offers 4 cozy bedrooms with a mix of queen, full, twin, and bunk beds. With WiFi, a ...
Click For PricingVRBO
- From $128 per night (USD)
Expedia
Charming 2-bedroom country house with AC, WiFi in Winter Haven
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Escape to this marvelous 2-bedroom Winter Haven country house retreat. With a cozy full bed and a comfy twin bed, guests ...
From $128 per night (USD)Expedia
- Click For Pricing
VRBO
Cozy 3 bedroom central hideaway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy quick and easy self check in with lock box system. Beautiful, quiet and secure community. Enjoy spacious and elega ...
Click For PricingVRBO
- From $259 per night (USD)
Expedia
- HIDDEN GEM - Spacious, minimal and clean! Legoland + Disney
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Consider this house your home away from home while you visit Florida! This fantastic property boasts 4 bedrooms, inclu ...
From $259 per night (USD)Expedia
- From $71 per night (USD)
VRBO
Cozy 1-bedroom mobile home with WiFi, AC in enjoyable Winter Haven
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Escape to this delightful mobile home in picturesque Winter Haven. This cozy retreat offers a bedroom, WiFi, and AC for ...
From $71 per night (USD)VRBO
- From $547 per night (USD)
VRBO
Lake View, Game Room, 10 minutes to Legoland - Perfect for Large Families!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 11
Welcome to The Elby, a fully renovated 1940's lake home with spacious rooms, modern amenities, and indoor and outdoor ga ...
From $547 per night (USD)VRBO
- From $257 per night (USD)
VRBO
Large 3\/1 Near DownTown and Dining
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Welcome to our spacious and modern retreat, perfectly situated in the heart of the city. This stylish home is designed ...
From $257 per night (USD)VRBO
- Click For Pricing
Expedia
5 Bedroom Chain of Lakes Home w\/AC Pet Friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 16
Bring the wwireless network kitchen for cooking air conditioner television washing machine supporting facilities free pa ...
Click For PricingExpedia
- From $111 per night (USD)
VRBO
Vintage Love Studio
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Come and souk up the uniqueness and custom build of this vintage place, turned into a luxurious oasis. This is a cozy st ...
From $111 per night (USD)VRBO
- From $281 per night (USD)
VRBO
Lake Shipp House with pool and dock on the water
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fully furnished single story home on Lake Shipp; has boat dock, inground heated swimming pool. Two bedrooms (king & quee ...
From $281 per night (USD)VRBO
- From $116 per night (USD)
VRBO
Updated 2 Bedroom Condo On Lake Lulu
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Conveniently locate in Winter Haven one mile from Lego Land and Shopping. Two bed rooms, updated kitchen, balcony, commo ...
From $116 per night (USD)VRBO
- Click For Pricing
Expedia
Spacious 3 Bed, 2 Bath Home Near Legoland
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
About this space A gem in the Heart of Winter Haven. This brand new 3 bedroom, 2 bathroom home is fresh, clean and ready ...
Click For PricingExpedia
- From $317 per night (USD)
VRBO
Cheerful 4 Bed, 3 Bath Home with Screened Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
About this space This stylish place to stay is perfect for vacation. With 2 ensuite bedrooms plus 2 additional rooms and ...
From $317 per night (USD)VRBO
- From $132 per night (USD)
Expedia
Florida Beachy Palms 2\/1 Home. No Cleaning Fee!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
This property is a beautifully updated 2/1 home. Property comes equipped with a full kitchen, living room, smart TV, ce ...
From $132 per night (USD)Expedia
- From $442 per night (USD)
VRBO
Cheerful New Construction Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Bring the whole family to this great place with lots of room for fun. Winter Haven is the up and coming city. Boasting b ...
From $442 per night (USD)VRBO
- From $195 per night (USD)
Expedia
A lakeside sunset delight near Disney, Universal, Sea World, Busch, LegoLand
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
We are open after Milton and have full power. Here's the place to kick back, fish and recharge or to enjoy endless attr ...
From $195 per night (USD)Expedia
- From $202 per night (USD)
VRBO
Looking for Relaxation?Near Legoland and Disney
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Newly renovated 3 bedroom, 2 bathroom house located in a quiet neighborhood in Lake Alfred, Florida. House has own priva ...
From $202 per night (USD)VRBO
- From $316 per night (USD)
Expedia
Experience family fun! LEGOLAND® Florida just a 12-min drive
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
In this cozy town of Winter Haven, you'll find a beautiful 4-bedroom house that's just a short 12-minute ride away from ...
From $316 per night (USD)Expedia
- From $99 per night (USD)
VRBO
View Container 5*Centrally Located*Private Bed\/Bath
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
WELCOME! Lake Mariam Container Home sits on 2.6 acres of Lakefront Property. If hospitality & peace is what you want, ou ...
From $99 per night (USD)VRBO
- From $573 per night (USD)
Expedia
Waterfront Winter Haven Home with Dock & Hot Tub!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Your lakeside paradise awaits at this 4-bedroom, 3-bath Winter Haven vacation rental, perfect for your 'Sunshine State' ...
From $573 per night (USD)Expedia